Acetic Acid → HCID 11519172, compound

HRID 601537Notes

Reaction equation

HRID 601537 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:29])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH:25]=O)=[C:19]([O:27][CH3:28])[CH:18]=4)[CH:13]=[CH:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.CC(O)=O.[OH-].[Na+]>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:29])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][N:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)=[C:19]([O:27][CH3:28])[CH:18]=4)[CH:13]=[CH:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 57501772HCID 57501772, compound

Product 1

HCID 11519172HCID 11519172, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Dissolve 3-{4-[2-(4-chloro-phenyl)-4-oxo-4H-thiazolo[5,4-c]pyridin-5-yl]-2-methoxy-phenyl}-propionaldehyde (94 mg, 0.22 mmol) in 1,2-dichloroethane (2.2 mL) and add pyrrolidine (20 μL, 0.24 mmol), AcOH (19 μL, 0.33 mmol), and NaHB(OAc)3 (70 mg, 0.33 mmol). Stir the yellow solution at room temperature for 1 h, then add 1N NaOH (5 mL), and extract the mixture with CH2Cl2 (2×10 mL). Combine the organic portions, then dry, filter, and concentrate. Purify the crude material by flash chromatography, using 8% 2N NH3 in MeOH/CHCl3 as eluent, to give the title compound (75 mg, 71%). MS (ES+) 480.1 (M+1)+. 1H NMR (400 MHz, CDCl3): δ 8.03 (d, 2H, J=8.3 Hz), 7.48 (d, 2H, J=8.8 Hz), 7.43 (d, 1H, J=7.5 Hz), 7.25 (t, 1H, J=3.7 Hz), 6.97 (d, 1H, J=7.5 Hz), 6.93-6.88 (m, 2H), 3.83 (s, 3H), 2.70 (t, 2H, J=7.7 Hz), 2.60 (br s, 6H), 1.96-1.79 (m, 6H).

Workup

  1. extractionextract the mixture with CH2Cl2 (2×10 mL)
  2. customCombine the organic portions, then dry
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the crude material by flash chromatography

Sources & evidence

ORD record
ord-e7511184031348518b8e1de651123974
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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